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New indane derived aminoalcohols as chiral ligands for the catalytic enantioselective addition of diethylzinc to aldehydes

✍ Scribed by Lluís Solà; Anton Vidal-Ferran; Albert Moyano; Miquel A. Pericàs; Antoni Riera

Publisher: Elsevier Science
Year: 1997
Tongue: English
Weight: 565 KB
Volume: 8
Category: Article
ISSN: 0957-4166
DOI: 10.1016/s0957-4166(97)00163-8

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✦ Synopsis

Secondary amines react with (IR,2S)-indene oxide 1 in a completely regioselective manner leading to trans-2-dialkylamino-l-indanols 4a-d in high yield. A Mitsunobu inversion via the corresponding p-nitrobenzoates, followed by reduction with DIBALH leads to the cis-2-dialkylamino-l-indanols 5a-d also in high yield. These two new classes of aminoindanols have been tested as chiral ligands for the enantioselective addition of diethylzinc to both aliphatic and aromatic aldehydes, leading to l-substituted l-propanols with up to 80% e.e. A very simple procedure t-or the enantiomeric enrichment of 1 from 88% to >_99% e.e. is also reported. @ 1997

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